The triisopropylsilyl effect: exceptional Cram-type selectivity in Mukaiyama aldol reactions of a silyl ketene thioacetal

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Anthony P. Davis, Stephen J. Plunkett and Jayne E. Muir


Abstract

The level of 1,2-asymmetric induction in the BF3·OEt2-promoted addition of silyl ketene thioacetals to α-asymmetric aldehydes is affected by the bulk of the silyl group; unprecedented Cram-type selectivity is given by the triisopropylsilyl derivative 8a.


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